MS CHAUHAN ADVANCE

200 OH 33. OsO4 X+Y 12 : 1 Product (X) will be : OH OH OH (a) OH OH O (d) O (b) (c) OH OH 34. CH == CH Br2 A 2NaNH2 B H2 C CCl4 Pd/CaCO3 Product (C) is : (a) Ph C == C H (b) Ph C == C Ph (c) Ph C == CH2 (d) Ph — C ºº C — Ph H Ph H H Ph 35. MMPP(one-equivalent) X 74% Ethanol MMPP ¾® Magnesium mono peroxy phthalate. Product (X) is : (a) O (b) O OH (c) HO (d) HO OH OMe 36. MCPBA P ; Product (P) is : O OMe 75% (a) OMe O O (b) O O https://t.me/studyzee

201 OMe (c) (d) None of these O OO CH3 CH3 OO 37. N Os N KOH A; Product (A) is : Mannitol/Water OO Cyclic osmate ester complexed with pyridine (a) HO CH3 (b) CH3 CH3 CH3 OH OH OH (c) (d) CH3 CH3 O CH3 38. + CBrCl 3 ¾¾hn ® ( A) (no ring substitution) Product (A) is : (b) Ph — CH 2 — Br (d) Ph — CH 2 — CBrCl 2 (a) Ph — CH 2 — Cl (c) Ph — CH 2 — CCl 3 39. MCPBA (A) ; MCPBA ¾® metachloroperbenzoic acid Product (A) of the above reaction is : (b) O (a) O (c) OH HO (d) https://t.me/studyzee

202 HO (d) 40. The major product of the following reaction sequence is : ¾ 2¾. H1¾.2BO2¾2H, 6H¾¾O ® ? OH OH O H (a) (b) (c) 41. Which one of the following compounds gives acetone (CH 3)2C == O as one of the product of its ozonolysis ? (a) (b) (c) (d) 42. Addition of HCl to 3, 3-dimethyl-1-butene yields two products, one of which has a rearranged carbon skeleton. Among the following carbocations, select the possible intermediates in that reaction ? ++ + + (CH 3)3CCHCH 2Cl (CH 3)3C C HCH 3 (CH 3 ) 2 C C(CH 3 ) 2 (CH 3) 2 C CH(CH 3) 2 | Cl 12 34 (a) 1, 2 (b) 1, 3 (c) 1, 4 (d) 2, 3 (e) 2, 4 43. Conversion of cyclohexene to cyclohexanol can be conveniently achieved by : (a) NaOH + H 2O (b) Br2 — H 2O (c) hydroboration, oxidation (d) hydroboration hydrolysis 44. Trans-cyclohexane-1,2-diol can be obtained by the reaction of cyclohexene with : (a) KMnO 4 (b) OsO 4 (c) peroxy formic acid /H 3O + (d) SeO 2 45. Bromination of (E)-2-butenedioic acid gives (a) (2R, 3S)-2, 3-dibromosuccinic acid (b) (2R, 3R)-2, 3-dibromosuccinic acid (c) a mixture of (2R, 3R) and (2S, 3S)-2, 3-dibromosuccinic acid (d) (2S, 3S)-2, 3-dibromosuccinic acid 46. The major product formed during the reaction of 1-methyl cyclopentene with CH 3CO 3H is CH3 CH3 CH3 CH3 (a) (b) OH (c) O (d) OH OH CH — CO 2H N¾aO¾H ® electrolysis || 47. ¾ ( A) ¾¾¾¾¾® ( B); Product (B) of the reaction is : CH — CO 2H (two mole) (a) CH 3 — CH 3 (b) H 2C == CH 2 (c) H — C ºº C — H (d) CH 2 == CH — CH == CH 2 https://t.me/studyzee

203 48. O–H O (Br¾om¾NolaaHBc¾rtCo2On¾i3za®tion)(Claycclitcoensteer) (a) HO OO (b) O O Br CO2H Br (c) OH Br (d) O O 49. ¾(¾1) ¾(CF¾3CO¾2 )2¾Hg¾, CH¾3C¾H2O¾H ® (P) ; Product (P) is : (2) NaBH4, HO - (100%) Cyclohexene OH OEt OEt OH OCH2CH3 (a) (b) (c) (d) OH 50. What is the major product expected from the following reaction ? ¾¾HKOM¾–ncOo¾4ld ® OH OH OH OH O OH H H (a) (b) OH (c) H (d) H OH 51. CH 3 - CH == CH 2 ¾(¾loBw¾r2coh¾nnc¾.)® (A) ; Product (A) of the reaction is : (a) CH 3 —CH — CH 2 — Br (b) H 2C == CH — CH 2 — Br | Br (c) CH 3 —C == CH 2 (d) Br — CH 2 — CH 2 — CH 2 — Br | Br OO Et – CH – C Et – CH – C ; Reagent (A) in the reaction is : 52. O AO CH2 – CH CH2 – CH C == CH2 C == O CH3 CH3 (a) O 3 Zn(H 2O) (b) HIO 4 (c) CrO 3 (d) Cold dil. KMnO 4 https://t.me/studyzee

204 CH3 53. ¾¾2.1N.¾OaHsO¾SO4¾3 ® Product of the reaction is: CH3 CH3 CH3 OH OH CH3 (a) CH3 (b) OH OH (d) H CH3 OH (c) CH3 CH3 H CH3 OH 54. Which compound is a possible product from addition of Br2 to 1-butene ? Br (b) Br (a) Br Br (c) Br Br (d) Br Br 55. Addition of Br2 to cis-2-butene would give a product which is: (a) achiral (b) racemic (c) meso (d) optically active 56. Addition of Br2 to trans-2-butene would give a product which is: (a) achiral (b) racemic (c) meso (d) optically active 57. Addition of OsO 4 to cyclopentene would give a product which is: (a) achiral (b) racemic (c) meso (d) optically active 58. Addition of BH 3 followed by H 2O 2 to trans-2-butene would give a product which is: (a) achiral (b) racemic (c) meso (d) optically active CH3CHCH = CH2 CH3CH – C|HCH3 OH A ; Reagent A may be : 59. (a) H 2O H + (b) BH 3.THF H 2O 2 - OH - (c) Hg(OCOCH 3)2.H 2O NaBH 4 .NaOH (d) All are possible 60. The major product of the following reaction is : CH 3 — CH == CH 2 + HBr ¾(¾C 6¾H5C¾O)2¾O 2¾pe¾roxi¾de ® (a) CH 3 — CH 2 — CH 2 — Br (b) CH 3CH(Br) — CH 3 (c) BrCH 2 — CH == CH 2 (d) Br HO 61. HO ¾¾HO2O3¾2 ® ( A) ¾-¾H2O® ( B) D Identify (B) : https://t.me/studyzee

205 OO OO (a) (CH2)5 — CO2H (b) (CH2)5 — CO2H HO HO OO (c) OO (d) HO (CH2)3 — CO2H HO (CH2)4 — CO2H 62. Which of the following is a major product of the reaction shown below? CH3 ¾¾HB2r¾O2 ® CH3 CH3 CH3 CH3 OH (a) Br (b) Br (c) Br OH OH (d) H H H H OH Br 63. In methyl alcohol solution, bromine reacts with ethylene (ethene) to yield BrCH 2CH 2OCH 3 in addition to 1, 2-dibromoethane because (a) the methyl alcohol solvates the bromine (b) the ion formed initially may react with Br - or CH 3OH (c) this is a free radical reaction (d) the reaction follows Markovnikov's rule 64. Which of the following compound was the starting material for the oxidation shown below ? ? ¾¾KMn¾O 4¾H¾+ ® HO O + CO2 O OH OH || O (a) (b) (c) (d) 65. Which series of reactions will achieve the following transformation ? Br 1 ¾¾1 ® ¾¾2® Cl 2 (a) Cl 2 CCl 4 2 Cl Cl 2 CCl 4 (c) Cl 2 CCl 4 Br2 1 Cl 2 CCl 4 NBS/hv (b) HBr (d) NBS/hv https://t.me/studyzee

206 66. Taking into account the stability of various cycloalkanes and carbocations, as well as the rules governing mechanisms of carbocation rearrangements, what is the most likely product of this reaction ? H–I ¾® ? II (a) (b) I I (c) (d) 67. A triene is treated with ozone followed by zinc in acetic acid to give the following three products. What is the structure of the triene ? O O H O O Products = H H O H H H O (a) (b) (c) (d) 68. Which of the following compound would yield trialkylborane shown below when treated with BH 3 THF ? B (a) 2-methylbut-1-ene (b) 2-methylbut-2-ene (c) 3-methylbut-1-ene (d) 3-methylbut-1-yne 69. If the following compound is treated with Pd/C in excess of hydrogen gas, how many stereoisomers of the product will be obtained ? https://t.me/studyzee

207 (a) 1 (b) 2 (c) 3 (d) 4 70. Which is the most precise designation of stereochemistry for the products formed in the electrophilic addition of DBr to 1-methylcyclohexene ? (D = 2H, an isotope of hydrogen) Br Br CH3 CH3 (a) (b) D D Br CH3 (c) (d) both (a) and (b) H 71. Consider the addition of HBr to 3,3-Dimethyl-1-butene shown below. What is the best mechanistic explanation for the formation of the observed product ? CH3 HBr H CH3 | C CH3 CH3 — C — CH == CH2 H3C C | H3C Br CH3 (a) Protonation of the alkene followed by a hydride shift and addition of bromide to the carbocation (b) Double bond shift in the alkene following by the protonation and addition of bromide to the carbocation (c) Addition of bromide to the alkene followed by a double bond shift and protonation (d) Protonation of the alkene followed by a methyl shift and addition of bromide to the carbocation 72. Propene CH 3CH == CH 2 can be converted into 1-propanol by oxidation. Indicate which sets of reagents amongst the following is ideal to effect the above conversion ? (a) KMnO 4 (alkaline) (b) Osmium tetroxide (OsO 4 CH 2Cl 2) (c) B 2H 6 and alk. H 2O 2 (d) O 3 Zn 73. Which is the most suitable reagent among the following distinguish compound (3) from the others ? (1) CH 3C ºº C — CH 3 (2) CH 3CH 2 — CH 2 — CH 3 (3) CH 3CH 2C ºº CH (4) CH 3CH == CH 2 (a) Bromine in carbon tetrachloride (b) Bromine in acetic acid solution (c) Alk. KMnO 4 (d) Ammonical silver nitrate 74. The principal organic product formed in the reaction given below is : CH 2 == CH(CH 2) 8 COOH + HBr ¾¾pero¾xi¾de ® .... (a) CH 3 — CHBr(CH 2)8 COOH (b) CH 2 == CH(CH 2)8 COBr (c) CH 2BrCH 2(CH 2)8 COOH (d) CH 2 == CH(CH 2)7 CHBrCOOH https://t.me/studyzee

208 75. When 2-butyne is treated with H 2/Pd – BaSO 4 ; the product formed will be : (a) cis-2-butene (b) trans-2-butene (c) 1-butene (d) 2-hydroxy butane 76. In the reaction, CH 3C ºº C — CH 3 (i) X CH 3 — C— C— CH 3 , X is : || || ¾(¾ii) ¾Zn ¾H2¾O ® OO (a) HNO 3 (b) O 2 (c) O 3 (d) KMnO 4 77. Which of the following alkene on catalytic hydrogenation given cis and trans-isomer ? (a) H2C CH3 (b) H3C CH3 CH3 H (c) CH3 H (d) all of these CH3 78. In the reaction of hydrogen bromide with an alkene (in the absence of peroxides), the first step of the reaction is the ................. to the alkene. (a) fast addition of an electrophilic (b) slow addition of an electrophile (c) fast addition of a nucleophilic (d) slow addition of a nucleophile 79. Which of the following alcohols cannot be prepared from hydration of an alkene ? OH (b) OH (a) (c) OH OH (d) 80. Which of the species shown below is the most stable form of the intermediate in the electrophilic addition of Cl 2 in water to cyclohexene to form a halohydrin ? H (a) O+H + (b) H Cl + H (c) (d) Cl Cl H · 81. The reaction, (CH 3)2C == CH 2 + Br · ¾® (CH 3)2 C - CH 2Br is an example of a/an ................ step in a radical chain reaction. (a) initiation (b) termination (c) propagation (d) heterolytic cleavage https://t.me/studyzee

209 82. Which of the following most accurately describes the first step in the reaction of hydrogen chloride with 1-butene ? (a) Cl – H ¾® + +Cl• (b) Cl – H ¾® + Cl– (c) Cl – H ¾® + +Cl– (d) H – Cl +H– + ¾® Cl 83. Which of the following best describes the flow of electrons in the acid-catalyzed dimerization of (CH 3 )2 C = CH 2 ? CH3 H3C CH3 CH3 H2C == C (b) C ==CH2 H2C == C (a) +C H3C CH3 CH3 H3C CH3 CH3 H2C H2C == C C — CH2 CH3 H3C CH3 (d) H2C — C+ CH3 (c) H3C C == CH2 H3C 84. Hydroboration of 1-methylcyclopentene using B 2D 6, followed by treatment with alkaline hydrogen peroxide, gives Me Me Me Me OH D D OH (d) H (a) OH (b) H (c) D D H COOH OH H 85. ¾C¾BC¾rl24® HOOCCH(Br)CH(Br)COOH HOOC (X) (P) HOOC (Q) COOH ¾C¾BC¾rl24® HOOCCH(Br)CH(Br)COOH (Y) The correct statements with respect to the above pair of reactions are that (I) the reactions are stereospecific (II) (X) is erythro and (Y) is threoisomer (III) (X) is threo and (Y) is erythro isomer (IV) each of (P) and (Q) gives a mixture of (X) and (Y) (a) I and II (b) I and III (c) I and IV (d) II and IV https://t.me/studyzee

210 86. The products P and Q in the following sequence of reactions, are MeO ¾¾LNi,H¾E3t(O¾l¾H) ® P ¾(¾ii) ¾(-i)78O¾°C3(,¾1Meq¾euHiv¾M.)e¾¾2S ® Q Me MeO MeO2C MeO MeO (a) OHC Me (b) COMe MeO Me Me CHO (c) MeO CHO MeO COMe (d) MeO2C Me OHC Me Me 87. 4-Pentenoic acid when treated with I2 and NaHCO 3 gives : (a) 4, 5-diiodopentanoic acid (b) 5-iodomethyl-dihydrofuran-2-one (c) 5-iodo-tetrahydropyran-2-one (d) 4-pentenolyiodide OH 88. ¾¾H2S¾HO24O¾, 0°¾C ® ( A) ¾¾-H¾Cl ® (B); Product (B) of the reaction is: Cl (a) O (b) O (c) O (d) O CH = CH2 89. ¾C¾BC¾rl24® (A) ¾(¾i) a¾lc.¾KO¾H ® (B) ¾(¾i) N¾aN¾H¾2 ® (C) , Product (C) is : (ii) NaNH2 (ii) CH3 -Cl (Styrene) (a) Ph — C ºº CNa (b) Ph — CH 2 — C ºº CH (c) Ph — C ºº C — CH 3 (d) Ph — CH == C == CH 2 90. Which of the following will give a mixture of cis and trans-1,4-dimethyl cyclohexane, when undergo catalytic hydrogenation ? CH2 | (a) (b) (c) (d) both (a) & (b) || CH3 Cis-3-6 dimethyl cyclohexene 91. An optically active compound A with molecular formula C 8H14 undergoes catalytic hydrogenation to give meso compound, the structure of (A) is : CH3 CH3 CH2 – CH3 (a) (b) (c) (d) CH3 CH3 CH3 CH3 https://t.me/studyzee

211 CH3 — CH2 CH2– CH3 92. C == C + HBr ¾¾¾¾¾® Products R 2O2 CH3 CH3 (Per- oxide) How many products will be formed in above reaction ? (a) 2 (b) 4 (c) 3 (d) 6 93. C == C ¾ ¾HP¾t2 ® Product of the reacion is : CH3 D (a) Racemic (b) Diastereomers (c) Meso (d) Pure enantiomers 94. cis-2-butene ¾¾PeHro¾Bxrid¾e ® product ; Product of the reaction is : (a) Racemic (b) Diastereomer (c) Meso (d) E and Z isomer CH3 H H CH3 95. (a) (b) Rate of reaction towards reduction using (H 2 Pt) : (a) a > b (b) a = b (c) b > a (d) Reduction of given molecule is not possible R' O R CH 3¾-S¾-CH¾¾3 ® O H CC || 96. R ¾¾ Product A + CH 3 — S — CH 3 OO dimethyl sulfide Product A of the above reaction is : (b) R¢ — CHO O (d) both (a) and (b) || (a) R — C — R (c) R — CO 2H O C —O—O—H 97. CH3 CH3 Cl (MCPBA) Product; Product is : C == C CH2Cl2 HH MCPBA ¾® Metachloroperbenzoic acid https://t.me/studyzee

212 CH3 C—C H CH3 C— C CH3 (a) O CH3 (b) O H H H H CH3 H CH3 (c) C— C CH3 (d) C – C CH3 CH3 O HO CH3 H 98. ¾(¾1)¾BH¾3; T¾H¾F ® (A) ; Product of the reaction is : (2) H2O2, HO- CH3 CH3 CH3 CH3 H OH H H (a) H (b) H (c) OH (d) H OH H H CH3 99. CH 3 — CH == CH 2 ¾(¾1) ¾TH¾F : ¾BD¾3 ® (A) ; Product ( A) of the above reaction is: 100. ( 2)CH 3CO 2T 101. (a) CH 3 — CHD — CH 2D (b) CH 3 — CHT — CH 2T (c) CH 3 — CHD — CH 2T (d) CH 3 — CHT — CH 2D Optically active isomer (A) of (C 5H 9Cl) on treatment with one mole of H 2 gives an optically inactive compound (B) compound (A) will be : (a) CH 3 — CH — CH == CH 2 (b) Cl — CH — CH == CH — CH 3 | | CH2Cl CH3 (c) CH 3 — CH — CH 2 — CH == CH 2 (d) CH 3 — CH 2 — CH — CH == CH 2 | | An organic cComl pound C 4H 6 on ozonolysis give Cl Compound will be : HCHO, CO 2, CH 3CHO. (a) H 2C == CH — CH == CH 2 (b) CH 3 — CH == C == CH 2 (c) CH 3 — C ºº C — CH 3 (d) 102. ¾¾HCH¾O,¾H¾+ ® major product of this reaction is : H 2O (a) OH (b) OH (c) CH2 – OH (d) OH OH OH OH CH 3 OH 103. | ¾¾KM¾nO¾4 ® ( A) ¾¾H¾+ ® (B) ¾¾HB¾¾r ® (C) CH 3 — CH D ROOR | CH 3 Product (C) in the above reactions is : https://t.me/studyzee

213 H CH 3 || (a) CH 3 — C — Br (b) CH 3 — C — Br | | CH 3 CH 3 CH 3 | (c) CH 3 — CH — H (d) CH 3 — CH | | C H 2 -Br CH 2 - Br 104. CH3 105. | CH 3 — C == CH 2 + (CH 3 ) 2 CHCH 3 ¾¾2H73F¾K ® C 8H18( A) Unknown (A) in the above reaction is : (a) 2, 2, 3-trimethyl pentane (b) 2, 2, 4-trimethyl pentane (c) 2, 2-dimethyl hexane (d) n-octane OH ¾¾B¾r2 ® HBr + (P) ¾¾MeO¾¾H ® (Q) ; Product (Q) is : Cl O Cl (b) Br O (a) OMe CH3O O O OMe || (d) CH3 (c) CH 3 - C - OMe 106. ¾¾H¾+ ® ( A) ¾¾cold¾d¾il. ® (B) ¾C¾rO¾3 ® (C) 107. OH D KMnO 4 Product (C) of the reaction is: O (c) OH (d) O (a) (b) CHO O OO D Cl What is the major product expected from the following reaction ? CH3 CH3 ¾¾D -¾¾Cl ® Product H CH3 CH3 D (d) (a) H (b) D (c) H Cl Cl CH3 H H Cl https://t.me/studyzee

214 108. Choose the correct product of this reaction : ¾1¾. B¾r2 ® 2. H 2O (a) Br (b) CH2 – CH3 (d) CH2 – CH3 109. OH Br OH H Br (c) H Br H Br CH3 ¾¾21..HB¾2HO3¾2//TO¾HH¾F– ® A; Product A is: CH3 CH3 CH3 (d) CH3 (a) H (b) (c) OH H OH H OH OH H CH3 CH3 OH 110. ¾1¾. H¾g(O¾Ac¾)2,¾H2¾O ® Product; Product is : H 111. 2. NaBH4 H 112. CH3 CH3 CH3 OH OH (a) H (b) (c) CH3 (d) H OH Choose the correct product of the following reactions : O CH3 Cl OOH 1. CH3 2. H3O+ OH CH3 CH3 OH CH3 (a) CH3 (b) OH (c) OH (d) H CH3 OH CH3 H CH3 OH CH3 How many stereoisomeric tetrabromides will be formed in the following reaction ? ¾¾2¾Br2¾® CCl4 https://t.me/studyzee

215 (a) 2 (b) 3 (c) 4 (d) 6 113. How many stereoisomeric pentabromides will be formed in the following reaction ? 114. Br ¾¾2¾Br2¾® CCl4 (a) 2 (b) 3 (c) 4 (d) None of these ¾¾perHo¾Cxlid¾e ® (A) ¾¾EtOD¾N¾a ® (Z) (major) Identify (Z) in the above sequence of reactions : (a) (b) O CH3 (c) (d) OEt CH 3 — CH — CO 2K ¾¾ele¾ctro¾lys¾is ® | 115. (A) (Major) CH 3 — CH — CO 2K Major product (A) of the above reaction : (a) (b) (c) (d) 116. O OO O CH == CH2 CF3CO3H (A) (B) (only one enantiomer is taken) O Which of the following statement is correct about A and B ? (a) A and B are mixture of diastereomers (b) A and B are mixture of enantiomers (c) A and B are optically active (d) B is racemic mixture CH3 117. CH3O ¾¾NaB¾H¾4 ® A ¾O¾¾3 ® B ¾¾H2¾O ® (C) (one of the product) O H HO O Identify the product (C): https://t.me/studyzee

216 OO CH 2 — OH || || | (a) CH 3 — C — C — O — CH 3 (b) CH — OH | CH 2 — OH CHO CHO | | (c) CH — OH (d) CHOH | | CH 2 — OH CHO CHO ¾¾HO¾Q ® (X) ¾C¾H2¾=C¾H-¾PÅ Ph¾3B¾r¾s ® (Y) 118. OH Product (Y) of the above reaction is : (a) (b) OO CH == CH — CH3 CH == CH — CH2 — OH (c) (d) OH CH3 119. In the reaction Me — C ºº C — Et ¾¾Na/¾liq¾.NH¾¾3 ® P ¾¾Br¾2 ® (Q) ; then Q is : 120. CCl4 (a) A pure compound which is optically inactive due to internal compensation (b) A binary mixture which is optically inactive due to external compensation (c) A binary mixture which is optically active (d) A pure compound which is optically inactive due to absence of chiral centre (a) (b) (d) (c) Which (p-bond) will reduce first, when above compound undergoes catalytic hydrogenation ? (a) a (b) b (c) c (d) d 121. Compound A, which is a degradation product of the antibiotic vermiculine has following structure O CH CH2 O CH2 C || C CH == CH — C CH3 CH OCH3 O ( A) ¾¾H¾2 ® (B) ¬¾(CH¾3 )¾2S¾ ¬¾O¾3¾¾ (C) . Unknown (C) is: Pd C CH2Cl2 C11H18O2 C11H14O 4 C11H18O 4 https://t.me/studyzee

217 (a) CH3 CH2 CH== CH O C CH2 C C – O – CH3 CH2 CH2 O CH2 C CH2 CH2 CH2 C OCH3 (b) CH3 CH2 CH2 CH2 C CH2 CH2 O (c) CH3 C CH2 CH2 CH C OCH3 CH2 CH2 C CH2 | CH3 (d) None of these O O A B 122. O Reagent (A) and (B) in above reaction are : (a) A = RCO 3H , B = H 2O 2 (b) A = RCO 3H , B = HIO 4 (c) A = RCO 3H, B = O 3 (d) A = O 3, B = RCO 3H 123. Rank the following in the increasing order of rate of reaction with HBr . (P) O (Q) (R) HN (a) R > P > Q (b) R > Q > P (c) P > R > S (d) P > S > R 124. Select the reaction(s) that would result in the formation of 2-bromopropane. (I) CH 3CH == CH 2 + HBr ¾¾pero¾xid¾e ® (II) CH 3CH == CH 2 + HBr ¾C¾C¾l4 ® (III) CH 3CH 2CH 3 + Br2 ¾¾hn ® (IV) CH 3CH == CH 2 + Br2 ¾C¾C¾l4 ® (a) I and III (b) II and III (c) I, II, and III (d) I, II and III 125. Which of the following reactions generates the major product ? Ignore stereoisomerism. (a) + HBr ¾® Br https://t.me/studyzee

218 ¾(¾1) ¾Hg(¾(O2A)¾Nc)a2¾B, HH¾42O,¾TH¾F ® OH (b) OH (c) ¾¾ ¾OH(¾-1,) H¾BH2O¾32, ¾¾® (d) (2) H 2O ¾¾H2O¾, H¾2SO¾¾4 ® OH (e) ¾¾B¾r2 ® Br CCl4 Br 126. In the given selective hydrogenation which combination is incorrect ? (a) ¾¾H¾2 ® (W.C. = Wilkinsons catalyst) W.C. (b) ¾¾H¾2 ® (W.C. = Wilkinsons catalyst) W.C. (c) ¾¾H¾2 ® (d) 127. W.C. ¾¾H¾2 ® CH 2 — CH == CH — CH 3 D 1. NaNH2 2. TsO (A) ¾¾Na ¾NH¾3(¾l) ® (B) ¾¾MC¾PB¾A ® (C). Compound (C) in above sequence of reaction is : HH (b) O (a) (d) H O H (c) C O O || CH2– C https://t.me/studyzee

219 128. ¾¾HB¾r ® ( A) ; CH3 R2O2/hn Major product (A) is : Br (b) (a) Br CH3 (d) Br (c) 129. In the reaction given below, the product would be : 130. OH | CH 3 — CH == CH — CH 3 ¾¾H3O¾¾+ ® CH 3 — CH 2 —CH — CH 3 (a) a mixture of diastereomers (b) optically active (c) optically pure enantiomer (d) a racemic mixture Surprisingly, the reaction shown below goes through classical carbocation. What is the major product of this reaction ? Br + HBr ¾® (a) trans-1, 3-dibromocyclohexane (b) cis-1, 3-dibromocyclohexane (c) trans-1, 2-dibromocyclohexane (d) cis-1, 2-dibromocyclohexane 131. The major product of the reaction given below is : OH ¾¾B¾r2 ® ? OH H 2O OH (i) Br OH (ii) Br OH Br Br (iii) HO OH (iv) HO OH OH O CH2Br (v) CH2Br (vi) H (a) (i) and (ii) (b) (iii) and (iv) (c) (v) and (vi) (d) none of these https://t.me/studyzee

220 132. Which reaction will occur at the fastest rate ? Br (a) HBr (b) HBr Br Br (c) HBr (d) HBr Br Cl 133. ¾dr¾yNea¾the®r Above reaction is known as : (b) Wurtz fittig reaction (d) Kolbe electrolysis (a) Wurtz reaction 134. (c) Fittig reaction 135. O || CH 3 ¾ CH 2 ¾ C ¾ H ¾R¾ed¾P +¾HI® A Product A is : (b) propanol (c) prapanoic acid (d) propene (a) propane Which of the following compound give diastereomers when treated with Br2 in CCl 4? (a) (b) (c) (d) CH2 CH3 H CH3 H CH3 Methylcyclopentane 1-Methylcyclopentene 3-Methylcyclopentene 4-Methylcyclopentene 136. A mixture of C 2H 6 , C 2H 4 and C 2H 2 is bubbled through alkaline solution of copper (I) 137. chloride, contained in Woulf’s bottle. The gas coming out is : (a) original mixture (b) C 2H 6 (c) C 2H 6 and C 2H 4 mixture (d) C 2H 4 and C 2H 2 ¾¾H+® Possible products ¾¾Br2¾CC¾l4 ® ( y) products D OH (x) The number of possible products for x and y is : (a) 2, 4 (b) 3, 5 (c) 3, 6 (d) 3, 4 https://t.me/studyzee

221 138. Select the incorrect statement : 139. (a) Bromine is more selective and less reactive (b) Chlorine is less selective and more reactive (c) Benzyl free radical is more stable than 2° free radical (d) Vinyl free radical more stable than allyl free radical Which of the following compound does not evolve CO 2 gas, when undergo oxidative ozonolysis ? (a) (b) (c) H 2C == CH — CH == CH 2 (d) 140. cis-3-hexene ¾(¾¾a)® meso 3,4-hexanediol trans-3-hexene ¾(¾¾b)® meso 3,4-hexanediol. Choose pair of reagent (a, b) for above conversions. (a) Cold KMnO 4 ,OsO 4 (b) Cold KMnO 4 , RCO 3H H 3O Å (c) RCO 3H H 3O Å , cold KMnO 4 (d) None of these 141. ¾¾N¾a ¾®( A) ¾O¾¾3 ®(B) ¾¾Ph3¾P==¾CH¾2(2¾mo¾l¾e) ®(C) 142. Liq. NH3 Zn Product (C) of the above reaction is : (b) 1,4-pentadiene (d) 1,3-heptadiene (a) 1,3-hexadiene (c) 1,3-butadiene How many carbon-hydrogen bond orbitals are available for overlap with the vacant p-orbital in ethyl carbocation ? (a) 0 (b) 3 (c) 5 (d) 6 143. To achieve above conversion, the reagents used will be : (a) O 3 H 2O 2 , HO - D (b) HBr, alc. KOH, O 3 ,LiAlH 4 ,H + D (c) HBr, t-BuOK, O 3 , KMnO 4, D (d) HCl, KMnO 4(cold), H + D O 144. ¾¾HgA(¾cOOAH¾c¾)2 ® X (major); Product ( X ) is: https://t.me/studyzee

222 OO O O (a) (b) (c) (d) H OH OH OAc HgOAc HgOAc OAc 145. Decreasing order of heat evolved upon catalytic hydrogenation of given reactants with a H 2 (Pd/C) is : (a) (b) (c) (d) (a) b > c > a > d (b) d > a > c > b (c) d > c > a > b (d) c > b > c > d 146. (a) (b) (c) (d) The correct order of heat of hydrogenation of given molecules is : (a) d > c > a > b (b) d > c > b > a (c) b > a > c > d (d) d > a > c > b 147. OH 1. Hg(OAc)2 A 2. NaBH4 O Product (A) of the above reaction is : (c) OO O (d) (a) (b) CH3 148. C CH2 + HBr A Product (A) is : (Major) Br Br Br (d) (a) Br (b) (c) https://t.me/studyzee

223 149. ¾C¾HCB¾lr4 ® Product; Comment upon optical activity of the product. 150. (a) Racemic mixture (b) Diastereomers (c) Meso (d) Optically inactive due to absence of chiral center CH3 | CH 3 — C == CH — CH 3 ¾H¾g(¾OA¾c)2¾/Et¾O¾H ® ( A) ( 90%) Product (A) of the above reaction is : C| H 3 CH 3 | (a) CH 3 — C — CH — CH 3 (b) CH 3— C — CH — CH 3 | | | | HgOAc OEt OEt HgOAc CH 3 C| H 3 | (c) CH 3— C — CH — CH 3 (d) CH 3 — C — CH — CH 3 | | | | OH HgOAc HgOAc OH 151. Me 2CH — CH — Me ¾3A¾5l20O¾¾°C3 ®( A) ¾(ii()¾i)A¾gHOI ®H (B) | 152. OH 153. Product (B) of above reaction : (a) Me 2C(OH)CH 2Me (b) Me 2CH — CH — Me | OH (c) Me — CH — CMe 3 (d) HO — CH 2 — (CH 2 )Me | OH In which of the following reaction, Markownikoff's rule is violated ? (a) CH 3 — O — CH == CH 2 ¾C¾HCB¾lr4 ® (b) CH 3 — NH — CH == CH 2 ¾C¾HCB¾lr4 ® (c) CH 3 —S— CH == CH 2 ¾ ¾HB¾r ® (d) O 2N — CH == CH 2 ¾ ¾HB¾r ® CCl4 CCl4 Decreasing order of rate of reaction of molecules towards electrophilic addition reaction is : CH == CH2 CH == CH2 CH == CH2 CH == CH2 NO2 OH CH3 NH2 (a) (b) (c) (d) https://t.me/studyzee

224 154. (a) a > b > c > d (b) b > c > a > d (c) d > b > c > a (d) b > d > c > a 2 CH 3 — C == CH 2 ¾H¾-¾A (a¾ci¾d)® ( A) (b) | (major) Ph Ph Product (A) is : Ph (a) Ph (c) (d) Ph CH3 155. ¾H¾¾D+ ® ( A) ¾R¾O¾H ® (B) Ph OR O CH2 — OH HÅ (major) Product (B) of the above reaction is : OR (a) (b) O O OR (c) (d) O OR O O 156. Which of the following compounds gives the same carbocation on ionization ? Br Br Br Br 2 3 4 1 (b) 2 and 4 (d) 1 and 4 (a) 1 and 3 (c) 1 and 2 157. For the following reactions the major products are shown : H 2C == CH — CH == CH 2 ¾¾HB¾r ® H 2C == CH— CH — CH 3 ¾+ ¾25°®C CH 2CH == CHCH3 | | 0°C Br Br These provide an example of ¾¾1 ¾ control at low temperature and ¾¾2 ¾ control at higher temperature. 1 2 12 (a) kinetic thermodynamic (c) kinetic kinetic (b) thermodynamic kinetic (d) thermodynamic thermodynamic https://t.me/studyzee

225 158. What is the product of 1, 4-addition in the reaction shown below ? HCl (a) (b) Cl Cl Cl (c) Cl (d) 159. CH3 H H OH Dehydration of the above compound will give : (a) meso product (b) racemic mixture (c) diastereomer (d) optically pure enantiomer CH2 - CH3 160. H Cl ¾C¾HCB¾lr4 ® CH = CH2 What is stereochemistry of product ? (b) Optically inactive (a) Racemic mixture (d) Meso product (c) Diastereomers 161. OH H2 AH CH3 O End product formed in the above reaction is : (a) Optically active (b) Racemic (c) Meso (d) Diastereomer 162. How many moles of BH 3 are needed to react completely with 2 mole of 1-pentene in 163. hydroboration-oxidation reaction ? (a) 2 mole (b) 3 mole (c) 2 3 mole (d) 3 2 mole OCH3 H3O+ Li A B Liq. NH3 Product (B) in the above reaction is : OH OO OCH3 (a) (b) (c) (d) OH OCH3 https://t.me/studyzee

226 164. 14 == CH — CH 3 ¾ l¾ow¾con¾c. o¾f B¾r2 ® ( ?) H 2C or high temp Product of the above reaction is : 14 14 (b) H 2C == C H — CH 2 — Br (a) H 2C == CH — CH 2 —Br 14 (c) CH 2 —CH —CH 3 (d) both (a) and (b) | | Br Br 165. In which of the following reactions 1,3-butadiene will be obtained as a major product ? 166. (a) Br — CH 2 — CH 2 — CH 2 — CH 2 — Br ¾(¾CH¾3 )3¾COK¾(2¾mo¾le)® (CH3 )3COH (b) HO — CH 2 — CH 2 — CH 2 — CH 2 — OH ¾C¾on¾c. H¾2SO¾4 ® (c) H 2C == CH — C ºº CH ¾H¾2(¾1mo¾¾le)® Ni 2 B (d) All of these Cl2 1. H2O H+ A ; Identify A. CH3 20°C 2. Ca(OH)2 D H2C C CH3 CH3 (a) CH3 C CH2 (b) CH 3 - CH - CHO O | O CH3 || CH3 (c) CH 3 — C — CH 2 — CH 3 | (d) CH 3 — C == CH 2 167. H2SO4 A; D OH Product (A) is : (a) (b) (c) (d) https://t.me/studyzee

CH3 d c NBS A (major) 227 (d) d 168. b 169. H a CH3 Bromination take place at : (a) a (b) b (c) c Which is incorrect statement about heats of combustion ? (a) > > (b) > > (c) Iso-butene > trans-2-butene > 1-butene (d) n-Hexane < n-Heptane < n-Octane 170. Predict the major product of the reaction. CH 3 Cl O (Product) | CH 3 — C == C — CH 2 — CH == CH 2 COOH | H+ CH3 CH3 CH3 CH3 CH3 || || (b) CH 3 — C — C — CH 2 — CH == CH 2 (a) CH 3 — C == C — CH 2 — CH — CH 2 O O CH3 CH3 CH 3 CH 3 || || (d) CH 3 — C — C — CH 2 — CH == CH 2 (c) CH 3 — C == C — CH 2 — CH — CH 2 || | | OH OH OH OH 171. ¾c¾old¾di¾l. K¾Mn¾O¾4 ® Product of the reaction is: (a) Meso compound (b) Enantiomeric pair (c) Diastereomers (d) Optically pure enantiomer OH H HH HO – C HH C H CC C 172. CH3O C C CC C H H H HH HH H (A) O3 (dichloromethane) (CH3)2S Optically active + (B) Optically inactive https://t.me/studyzee

228 Product (A) of above reaction is: (a) CH 3O —CH — CH 2 — CH 2 — CHO | CO2H CO2H | (b) CH 3O — CH 2 — CH — CH 2 — CO 2H (c) CH 3O —CH — CH 2 — CH 2 — CO 2H | CO2H (d) CH 3O —CH — CH 2 — CH 2 — CH 2 — CHO | CO2H O 173. ¾H¾2 ¾(2-3¾atm¾)(1¾mo¾l¾e)® Products ; Comment up on optical activity of products. 10% Pd C 174. (a) Diastereomers (b) Racemic mixture (c) Meso (d) Optically pure enantiomer O + HBr ¾¾® Product (1 mole) Addition of a mineral acid to an olefin bond leads to major product, Identify it: O O Br (a) (b) Br Br O O (c) (d) Br 175. H2 (one mole) Product PtO2 In polyenes that contain differently substituted (C==C) double bonds, it is possible to hydrogenate chemeselectively one (C==C) double bond. Product is : (a) (b) (c) (d) https://t.me/studyzee

176. MCPBA Product 229 O OH (MCPBA ¾® meta-chloro perbenzoic acid) Stereochemistry of the product of above reaction is : (a) Meso (b) Racemic (c) Diastereomers (d) Optically inactive due to absence of chiral center. O 177. Conc. H2SO4 P Identify product (P). O (a) (b) O (c) O (d) H2SO4 B 178. A A isomerise to B on addition of traces of acid H 2SO 4. Compound (B) is : (a) (b) (c) (d) R OH 179. SOCl2 A pyridine, D Product (A) of the reaction is : https://t.me/studyzee

230 Cl R R R (a) (b) (c) (d) None of these OH 180. HO ¾H¾+ (¾exc¾es¾s)®( A). Product (A) is : OH D (a) (b) (c) (d) 181. Which of the following reactions do not represent the major product of given Birch reductions ? (i) Na Na liq. NH3 (ii) liq. NH3 CH3 CH3 CO2H CO2H Na Na (iii) liq. NH3 (iv) liq. NH3 Na (v) liq. NH3 Na (b) (iv), (vi), (vii) (d) (i), (ii), (v), (vii) (vi) liq. NH3 (vii) 2-butyne ¾ ¾N¾a¾® cis-2-butene liq. NH3 (a) (i), (iii), (vi) (c) (iv), (v), (vi) 182. ¾B¾H¾3 ® ¾H¾2O¾2, H¾O¾- ® ( A) OR Product (A) is: https://t.me/studyzee

231 OH OH (a) (b) OH(c) OH (d) OR OR OR OR OH Hint : Think carefully about the relative stabilization of developing positive charge, when the double bond reacts with an electrophile. 183. ¾H¾O¾Cl® ( A) ¾N¾aO¾¾H,® (B) H2O 70% B = cyclohexeneoxide 25°C B = anti-diol B = cyclohexeneoxide Correct statement about above reaction is: B = anti-diol (a) A = cis-2-chlorocyclohexanol, (b) A = trans-2-chloro cyclohexanol, (c) A = trans-2-chlorocyclohexanol, (d) A = cis-2-chlorocyclohexanol, 184. ¾ ¾H¾Å ® Predict the major product: O HO (a) (b) (c) (d) HO HO O 185. ¾H¾2S¾O¾4 ® ( A) ; Product (A) is : OH OH (a) (d) (Major ) OH (b) (c) Br 186. 82 Br - 82 Br ¾ ¾¾® Major product of the reaction is : (a) CCl4 H Br82 Br82 Br H (b) Br (c) Br82 (d) Br82 Br82 H H Br82 H Br82 Br82 Br https://t.me/studyzee

232 Br2 stereochemistry of the product is: 187. CCl4 H CH3 (b) Racemic mixture (a) Diastereomers (d) Pure Enantiomers (c) Meso 188. Br2 Product/s obtained is/are : CCl4 H CH3 (b) Racemic (a) Diastereomers (d) Optically pure enantiomers (c) Meso 189. ¾P¾h3¾P=C¾H¾2® ¾P¾h3¾P=C¾H¾2® ( x) ; Product ( x) is : O (b) (a) CH2 (d) (c) CH–CH3 CH3 | — OH ¾H¾¾+ ® ( A) ; 190. CH 3 — CH 2 — CH 2 — CH 2 —C — CH 2 Product (A) is : | D (major) CH3 (a) CH 3 — CH 2 — CH 2 — CH 2 —C == CH — CH 3 | CH3 (b) CH3—CH2—CH2—CH2—CH == C CH3 CH3 (c) CH 3 — CH 2 — CH 2 — CH 2 —C == CH 2 | CH3 CH3 | (d) CH 3 — CH 2 —CH — CH 2 —C == CH 2 | CH3 https://t.me/studyzee

233 191. CH 3 — CH == CH — CH 3 ¾R¾2HOB¾2r¾, D® (Anti-Markownikoff's addition) Comment on optical activity of the products: (a) Racemic (b) Diastereomer (c) Meso (d) Optically pure enantiomer 192. O || ¾C¾H3¾-C¾-O-¾O-¾H ® ( A) ; Product (A) is : (major ) (a) O (b) O (c) OH OH OH (d) OH RCO3H Racemic mixture H2O 193. A Cold dil. KMnO4 Meso-compound 194. (alkene) Alkene (A) will be : (a) cis-2-pentene (b) cis-2-hexene (c) cis-4-octene (d) trans-2-hexene O + PPh 3 ¾® ( A) + POPh 3 H Me (major) Me H Product (A) is (a) trans-2-butane (b) cis-2-butene (c) 1-butene (d) Iso-butene 195. In which of the following reactions, two products will be formed other than phosphonium ylide (POPh 3 ) O (a) + Ph 3P == CH 2 ¾® (b) CH 3CHO + Ph 3P == C — CH 3 ¾® | O CH3 || (c) Ph — C — H + Ph 3P == CH — Ph ¾® O || (d) H — C — H + Ph 3P == CH — CH 3 ¾® https://t.me/studyzee

234 196. To carry out the given conversions, select the correct option: O a R1 — C — R2 + R2CO2H R1 OO HO O C C b R1 — C — R2 + R2 — CHO R2 R2 c OH R1 — CH — R2 + R2 — CH2 — OH (a) a = Ag 2O, b = Zn CH 3CO 2H, c = LiAlH 4 (b) a = H 2O 2, b = CH 3 - S - CH 3, c = NaBH 4 (c) Both (a) and (b) (d) None of these 197. The product (A) of given alkoxymercuration de-mercuration is : CH3 ¾(¾1)H¾g(O¾2C¾CF3¾)2,¾CH¾3O¾H ® ( A) (2) NaBH4, HO- (major) OCH3 OCH3 OH OH (a) (b) (c) (d) ONa | 198. CH 3 —C == CH 2 ¾ ¾HC¾ººC¾¾H ® ¾ ¾H¾+ ® ¾ ¾ ¾H2¾¾® ¾ ¾Al2¾O¾3 ® Pd- BaSO4 D End product of the reaction is : (a) H 2C == CH —C == CH 2 (b) CH 3 — CH == CH — CH == CH 2 | (d) H 2C == CH — CH 2 — CH == CH 2 CH3 (c) H 2C == CH — CH == CH 2 199. Major product of the given reaction is : H 2C == CH — CH 2 — I ¾H¾I(Ce¾Cxlc4e¾s¾s)® (a) CH 3 — CH— CH 2 (b) CH 3 — CH — CH 3 | | | I II (c) CH 3 — CH 2 — CH 2 — I (d) I — CH 2 — CdH 2 — CH 2 — I https://t.me/studyzee

235 200. The rate constant for a reaction can be increased by a the stability of the reactant or by b the 201. stability of the transition state. Select the correct choice for a and b. (a) decreasing, decreasing (b) increasing, decreasing (c) decreasing, increasing (d) increasing, increasing Major product of the given reaction is : H 2C == CH 2 + CH2 ¾H¾¾+ ® Product D (a) (b) CH3 | (c) (d) H 2C = C -CH 2 - CH 2 - CH 3 O 202. + Ph 3P ==CH 2 ¾® ( A) Major Major product (A) is : (a) (b) (c) OH (d) 203. In the given reaction, only one alkene undergo preferential oxidation by electrophilic ozone. Identify product (P) of the given reaction: OMe ¾ M¾e2¾S, -¾78°¾CO3t¾hen¾N¾aBH¾4 ® (P) ( > 52%) (a) CO2Me CO2Me CHO (b) OH O || (c) CH 3 — C — CH 2 — CH == C — CH 2 — CHO | OMe OH | (d) CH 3 — CH — CH 2 — CH == C — CH 2 — CH 2 — OH | OMe https://t.me/studyzee

236 204. CH2—CH2—CH == CH2 ¾H¾¾Cl® (P) ; Product (P) is: (major) OH Cl Cl Cl (a) (b) (c) (d) 205. CO2H ¾ ¾ I¾2 ¾® ( A) ; Major product of the reaction is : (a) (c) NaHCO 3 I O (b) O OO I I O (d) O O O OH 206. OMe ¾P¾d-¾HBa2S¾O¾4 ® ( A) ¾H¾3O¾Å ® (B) Product (B) is : (b) Ph - CH = CH - CHO OH O | || (a) Ph - CH - CH = CH - CH 2 - C - H (c) Ph - (CH = CH)2 - CHO (d) Ph - (CH = CH)3 - CHO 207. Isobutene, in the presence of H 2SO 4, forms a mixture of two isomeric alkene (C 8H16). The major alkene is : CH 3 CH 3 CH 3 CH 3 | | | | (a) CH 3 — C — CH == C — CH 3 (b) CH 3 — C — CH 2 — C == CH 2 | | CH 3 CH 3 CH3 CH3 CH3 CH3 | | | | (c) CH 3 — CH — CH == CH — CH — CH 3 (d) CH 2 == C — CH 2 — CH 2 — CH — CH 3 https://t.me/studyzee

237 208. An unknown alkene (A) reacts with 3 mole of H 2 gas in presence of platinum catalyst to form 1-isopropyl-4-methyl cyclohexane. When unknown alkene (A) is ozonized and reduced, following product are obtained O O OO OO || || || || || || H — C — H, H — C —CH 2 — C — C — CH 3, CH 3 — C — CH 2 — C — H The alkene (A) is : (a) (b) (c) (d) O ¾¾H—¾|C|¾—C¾H¾\\/CCHH¾33 ® 209. (1) NBS A) (B) ¾O¾Hs2OO¾42 ®(C) ¾¾¾¾¾¾®( (2) Mg ether CH3 —CH2— Br Product (C) is : OEt OEt H (a) OH (b) OH OH OH OEt H (c) OH (d) Both (a) and (b) OH 210. The following reaction take place in high yields. CO2CH3 ¾¾Hg(¾OA¾c¾)2 ® Product D Use your knowledge of alkene chemistry to predict a product even though you have never seen this reaction before CO2CH3 H CO2CH3 (a) (b) HgOAc HgOAc https://t.me/studyzee

238 CO2CH3 CO2CH3 (c) (d) OH OH OO OO OO || || || || || || 211. ¾(¾1)O¾¾3 ® H — C — C— H+ CH 3 — C — C — CH 3 + CH 3 —C —C— H ( 2)Zn Glyoxal 2, 3- Butanedione Pyrualdehyde What is the ratio of glyoxal to pyrualdehyde obtained in the above reaction ? (a) 1 : 3 (b) 3 : 1 (c) 3 : 2 (d) 2 : 3 CH3 212. ¾¾liq.N¾NaH¾3 ®( A) ¾OZ¾¾n3 ® Products Which of the following product cannot be obtained in above reaction ? OO OO || || || || (a) H — C —CH 2 — C — H (b) CH 3 — C — CH 2 — C — H O || (c) CH 3 —CH — C— H (d) None of these | CHO 213. CH3 C == C CH3 + + — – + H 2O ¾O¾sO¾4 (1¾0-4¾m¾ole®) A + (CH 3 )3 N CH3 (CH 3 )3 N O CH3 TMAO (0.034 moles) 2, 3-dimethyl-2-butane (0.025 mole) (TMAO ® trimethyl amine -N - oxide) Product (A) is : CH3 C—C CH3 CH 3 CH 3 (a) CH3 || O (b) CH 3 — C — C — CH 3 CH3 || OH OH O O || || (c) CH 3 — C — CH 3 (d) CH 3 — C — C(CH 3 )3 https://t.me/studyzee

214. HO H3O+ A 239 OH Product (A) of the reaction is : OH (a) (b) (c) (d) None of these (b) 215. OH ¾¾H¾+ ® ( A) D (major) Product (A) is : (a) (c) (d) CH3 C == CH2 CH3 C == CH2 CH3 C == CH2 CH3O CH3OCH2 216. CH3 (a) (b) (c) Arrange the above in the decreasing order of reactivity towards HBr : (a) a > b > c (b) b > a > c (c) b > c > a (d) a > c > b https://t.me/studyzee

240 217. Which reaction has the lowest DG++ or (Activation-Energy)? HBr HBr (a) (b) Br Br HBr (d) HBr (c) Br Br 218. Which of the following will rearrange ? + + (1) (2) (3) (4) + + (a) 1 (b) 1 and 3 (c) All (d) 1, 2, 4, 219. Which of the following is most likely to undergo a favorable hydride shift ? (a) (b) (c) (d) 220. Energy profile diagram for dehydration of 2-butanol using conc. H 2SO 4 is given below : PE Å a cb OH Me – CH2 – CH | | Me – CH2 – CH – Me CH3 Reaction co-ordinate Product (b) of above reaction is : (a) 1-butene (b) cis-2-butene (c) trans-2-butene (d) iso-butene 221. How many alkene on catalytic hydrogenation given isopentane as a product ? 222. (a) 2 (b) 3 (c) 4 (d) 5 Which of the following would not rearrange to a more stable form ? + + (d) (a) + (b) H (c) + https://t.me/studyzee

241 223. Consider the following reaction. ¾S¾O¾2® CH2 —– CH2 + SbF6- BrCH 2CH 2F + SbF5 - 60°C + Br In this reaction SbF5 acts as: (a) an acid (b) a base (c) a nucleophile (d) an electrophile 224. ¾B¾r2 ¾h¾v ® Major (X) ¾ ¾Alc¾oho¾l¾ic ® Major(Y) ¾ ¾H¾-Br¾® Major(Z): KOH D Peroxide Product (Z) is: Br Br Br (a) (b) (c) (d) Br CH3—C ºº C—H NaNH2 CH3—I Li/liq NH3 (B) 225. (A) H2 (C) 226. Pd-CaCO3 Relation between (B) and (C) is: (a) Enantiomer (b) Diastereomer (c) Geometrical isomer (d) Meso The reaction of HBr with the following compound would produce : OH (a) OH Br OH Br (b) Br Br (c) Br Br (d) 227. + Br2 Br Br is an example of: 228. (a) Nucleophilic addition (b) Nucleophilic substitution (c) Electrophilic addition (d) Electrophilic substitution (e) Free radical substitution (b) Nascent hydrogen Olefins can be hydrogenated by : (d) Lithium hydride in ether (a) Zinc and HCl (c) Raney Ni and H https://t.me/studyzee

242 CH3 229. What are the products obtained on hydroboration-oxidation of the given alkene CH3 CH3 CH3 CH3 (I) (II) (III) (IV) H OH OH H OH CH3 H OH H CH3 (V) (VI) H OH HO (c) II and VI (d) III and V (a) I and III H (b) II and IV 230. CH3CH2CH == CH2 HBr (A) CH3CH2C ºº CH Hg(OAc)2 (C) NaBH4 (D) CCl4 B2H6 HBr (B) H2O2/OH R2O2 Relation between A and B, C and D are : (a) Position, chain (b) Position, Functional (b) Chain, Identical (d) Metamer, Functional 231. In which reaction syn addition doesn’t take place. (a) dil.KMnO4 Ni (b) D2 (c) (1) B2H6 (d) Br2 (2) H2O2/NaOH CCl4 232. Number of olefin of C 4H8 HBr Number of Markonikow product (including stereo) ¾® (x) (y) x + y is : (a) 5 (b) 6 (c) 7 (d) 8 https://t.me/studyzee

243 1. (c) 2. (d) 3. (c) ANSWERS — LEVEL 1 6. (b) 7. (c) 8. (c) 9. (c) 10. (d) 11. (b) 14. (b) 15. (b) 16. (c) 17. (d) 18. (d) 19. (b) 4. (d) 5. (b) 22. (a) 23. (b) 24. (b) 25. (b) 26. (b) 27. (d) 12. (d) 13. (c) 30. (b) 31. (c) 32. (b) 33. (a) 34. (b) 35. (b) 20. (d) 21. (b) 38. (b) 39. (b) 40. (b) 41. (d) 42. (e) 43. (c) 28. (b) 29. (d) 46. (c) 47. (c) 48. (b) 49. (b) 50. (b) 51. (b) 36. (b) 37. (b) 54. (d) 55. (b) 56. (c) 57. (c) 58. (b) 59. (c) 44. (c) 45. (a) 62. (d) 63. (a) 64. (b) 65. (d) 66. (b) 67. (d) 52. (a) 53. (b) 70. (d) 71. (d) 72. (c) 73. (d) 74. (c) 75. (a) 60. (a) 61. (b) 78. (b) 79. (d) 80. (d) 81. (c) 82. (b) 83. (a) 68. (a) 69. (c) 86. (d) 87. (b) 88. (b) 89. (c) 90. (d) 91. (b) 76. (c) 77. (d) 94. (a) 95. (a) 96. (d) 97. (b) 98. (a) 99. (c) 84. (a) 85. (a) 102. (b) 103. (d) 104. (b) 105. (b) 106. (c) 107. (b) 92. (b) 93. (a) 110. (d) 111. (c) 112. (b) 113. (a) 114. (b) 115. (c) 100. (d) 101. (b) 118. (b) 119. (b) 120. (d) 121. (b) 122. (c) 123. (a) 108. (b) 109. (d) 126. (a) 127. (b) 128. (c) 129. (d) 130. (a) 131. (c) 116. (a) 117. (b) 134. (a) 135. (d) 136. (c) 137. (b) 138. (d) 139. (d) 124. (b) 125. (d) 142. (b) 143. (b) 144. (b) 145. (b) 146. (c) 147. (b) 132. (d) 133. (c) 150. (b) 151. (a) 152. (d) 153. (c) 154. (c) 155. (b) 140. (b) 141. (b) 158. (a) 159. (b) 160. (c) 161. (b) 162. (c) 163 (b) 148. (a) 149. (d) 166. (b) 167. (b) 168. (a) 169. (c) 170. (b) 171. (b) 156. (c) 157. (a) 174. (c) 175. (b) 176. (b) 177. (b) 178. (c) 179. (b) 164. (d) 165. (d) 182. (b) 183. (c) 184. (c) 185. (c) 186. (b) 187. (a) 172. (d) 173. (b) 190. (b) 191. (a) 192. (b) 193. (c) 194. (b) 195. (c) 180. (c) 181. (b) 198. (a) 199. (b) 200. (c) 201. (c) 202. (c) 203. (b) 188. (b) 189. (b) 206. (c) 207. (b) 208. (b) 209. (b) 210. (b) 211. (c) 196. (c) 197. (b) 214. (a) 215. (b) 216. (b) 204. (d) 205. (b) 212. (c) 213. (b) 217. (d) 218. (c) 219. (a) 220. (b) 221. (b) 222. (c) 223. (d) 224. (c) 225. (b,c) 226. (b) 227. (c) 228. (c) 229. (d) 230. (b) 231 (d) 232. (c) * For question 56 and 57, option (a) is also correct. https://t.me/studyzee

244 Level - 2 1. Reagents A. HCl B. Br2 C. Hg(OAc)2 in H 2O D. B 2H 6(BH 3 ) in ether E. H 2O 2 F. KMnO 4 in H 2O G. HOBr H. NaBH 4 In each reagent box write a letter designating the best reagent and condition selected from the above list of reagents. Reactant Reagent Product (CH 3 )2 CHCH == CH 2 (i) (CH 3 )2 CHCH(Cl)CH 3 (ii) 3- methyl-1- butene (iii) 2-Chloro- 3- methyl butane (iv) (v) (CH 3 )2 CHCHBrCH 2Br 1, 2- dibromo- 3- methyl butane (CH 3 )2 CHCHOHCH 2Br 1, bromo- 3- methyl 2-butanol (CH 3 )2 CHCH(OH)CH 3 3- methyl- 2- butanol (CH 3 )2 CHCH(OH)CH 2OH 3- methyl- 1, 2- butanediol 2. Propene (CH3 — CH == CH2 ) can be transformed to compounds (a to j) listed in the left-hand column. Write letter designating the reagent, you believe will achieve desired transformation. In the case of a multi step sequence write the reagent in the order they are to be used. Desired Product No. of Write Reagent List Steps options a. CH 3CHBrCH 2Br one A. Hg(OAc)2 in H 2O b. (CH 3 )2 CHOH two B. B 2H 6 in THF https://t.me/studyzee

c. CH 3CH 2CH 2OH two 245 C. NaBH 4 in alcohol d. CH 3COCH 3 three D. Br2 in CH 2Cl 2 E. H 2O 2 in aqueous base e. CH 3CH 2CHO three F. HOBr (NBS in aqueous acetone) G. HBr in CH 2Cl 2 f. CH 3CH(OH)CH 2Br one H. OsO 4 in ether I. Thionyl chloride (SOCl 2) g. (CH 3 )2 CHBr one J. NaHSO 3 in aqueous acetone K. NaOH in alcohol and reflux h, k. CH 3CH(OH) CH 2OH two L. NaNH 2 (strong base) i. CH 3 - CH 2 - CH 2 - Cl three j. CH 3 - C º CH two https://t.me/studyzee

246 3. In each reaction box write a single letter designating the best reagent and condition selected from the list at bottom of the page. (F.S., ® first step, S.S ® second step, T.S. ® third step) Reaction Reactant Options Product CH3 F.S. OH CH3 1. S.S. OCH3 CH3 F.S. CH3 O 2. S.S. T.S. CH3 OH 3. F.S. OH S.S. O Ph 4. F.S. S.S. F.S. Ph 5. S.S. T.S. O A. NaBH 4/alcohol B. Ph - CO 3H/ C. PCC D. CH 3ONa/ CH 2Cl 2 CH 3OH E. B 2H 6 in THF F. H 2O 2/aq. NaOH G. H 3PO 4 & heat H. AlCl 3/C 6H 6 I. O 3 in CH 2Cl 2 J. Br2in CH 2Cl 2 K. 20% KOH & heat L. Ph - Li/ether https://t.me/studyzee

247 4. Match the reagents a-j with products A-J. There is one best product for each reaction. Br (x) The molecule (x) is the starting material for all reactions in problem. Do the ones you know first and then tackle the rest by deductive reasoning Products Reagents Option Br (a) H 2O heat, pH 7 HO HO O (b) OH AB F3C O OH OH tBuOK, polar aprotic solvent (c) C O (1) O 3, ether Br (d) (2) H 2O, NaOH, H 2O 2 O E (e) Br2 ,CCl 4 Br D Br (f) NBS, hv, CCl 4 O G (g) (1) H 3O(+) HO Br (2) NaOH, H 2O F Br OH Br Br (h) (1) BH 3 , ether (2) H 2O 2 H Br I (1) OsO 4 Br (i) (2) NaOH,H 2O Br Br J (j) H 2 Pd C(EtOH) https://t.me/studyzee

248 Column (II) 5. Match the column: (p) cis-product with H 2 / Pd - BaSO 4 (q) Trans-product with Na /liq. NH 3 Column (I) (r) White with amm. AgNO 3 (a) CH 3 ¾ C ºº C ¾ CH 3 (s) H 2 gas with Na (b) CH 3 ¾ CH 2 ¾ Cºº CH (c) CH 3 ¾ C ºº CH (d) CH 3 ¾ C ººC ¾ Et https://t.me/studyzee

249 6. Match the column I with column II and with column III (Matrix). Column-I Column- II Column- IIII Reaction Nature of product formed Number of chiral center present in product. (Consider only one isomer in case of racemic mixture or Diastereomer) (a) H ¾ B¾¾r2 ® (p) Racemic mixture (w) 0 CH3 1 CCl4 2 3 ¾ B¾¾r2 ® (q) Meso (x) (b) CCl4 (y) (z) H CH3 ¾ B¾¾r2 ® (r) Diastereomer (c) CCl4 (s) Vicinal dihalide CH3 (d) CH3 C == C H Br2 H CH3 CCl4 https://t.me/studyzee